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<h1><a href="https://archiveofourown.org/works/24948478">After A Prize To-Night</a> by <a class='authorlink' href='https://archiveofourown.org/users/plutonianshores/pseuds/plutonianshores'>plutonianshores</a></h1>

<table class="full">

<tr><td><b>Category:</b></td><td>Original Work</td></tr>

<tr><td><b>Genre:</b></td><td>Cunnilingus, F/M, Loss of Virginity, Regency, Vaginal Fingering, Vaginal Sex, could be read as underage, rapist pov</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>Completed</td></tr>

<tr><td><b>Published:</b></td><td>2020-07-05</td></tr>

<tr><td><b>Updated:</b></td><td>2020-07-05</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-05-04 08:41:04</td></tr>

<tr><td><b>Rating:</b></td><td>Explicit</td></tr>

<tr><td><b>Warnings:</b></td><td>Creator Chose Not To Use Archive Warnings, Rape/Non-Con</td></tr>

<tr><td><b>Chapters:</b></td><td>1</td></tr>

<tr><td><b>Words:</b></td><td>1,529</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/24948478</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/plutonianshores/pseuds/plutonianshores</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>A highwayman slips away from one disastrous theft and finds an even finer jewel</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>Original Female Character/Original Male Character, Rakish highwayman hiding out at a house party noncons comely Regency teen</td></tr>

<tr><td><b>Comments:</b></td><td>5</td></tr>

<tr><td><b>Kudos:</b></td><td>78</td></tr>

<tr><td><b>Collections:</b></td><td>Nonconathon 2020</td></tr>

</table>

<a name="section0001"><h2>After A Prize To-Night</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Author's Note:</b><ul class="associations">
      <li>For <a href="https://archiveofourown.org/users/nothingbutregret/gifts">nothingbutregret</a>.</li>



    </ul></div><div class="userstuff module">
    
    <p>Tom slumped against the finely-papered wall, trying to temper his breathing. He wasn’t sure how this theft had gone so wrong. Lady Montrose was meant to be alone in her carriage, all of his reconnaissance had led him to believe her husband had other plans. And yet, there her husband had been, pistol and all. Tom had barely escaped without a few new holes shot into him, and he shuddered to think what would have happened had he not planned to rob Lady Montrose so close to her destination. At some point the Montrose carriage would arrive at the party, and they might muster a group to search for the rapscallion who’d attempted to steal her jewels, but in the meantime Tom might be able to make up his effort if any of the bedrooms had been left unsupervised during the party.</p><p>Footsteps in the hall made him tense and look around for a place to hide. One person, a high giggle echoing into the room as she stumbled. Well, perhaps he didn’t need to hide after all. He waited, listening for and not finding nay other sets of footsteps, before stepping out into the doorway.</p><p>"Oh!" the girl said, hand flying to the glittering necklace hanging down between her breasts. "You’re not Hugh Morton."</p><p>"I must confess," Tom said, sweeping into a bow, "I am not."</p><p>The girl was drunk, that much was clear. She was also beautiful, a plump face and ample bosom and perfect heart-shaped mouth. Likely a virgin too, albeit not likely to have remained one long if she’d been following the Morton boy away from the party. Well, Tom could give her a ride better than any prissy noble could manage.</p><p>"He asked to speak to me," she said, fingers worrying at the gold chain around her neck. "<em>Me</em>, if you’ll believe it, and he with 5,000 a year!" She paused, face wrinkling into an adorable regret. "Oh, I oughtn’t to have said that, terribly improper."</p><p>Tom very nearly felt sorry for her. The poor thing thought Morton wanted her hand in marriage, instead of a quick fuck and an unceremonious abandonment. "We don’t need to stand on propriety here." He extended his hand, kissing the girl’s when she gave it to him.</p><p>"I don’t think we’ve met?" The girl’s wide-eyed look was a picture of innocence. "I’m Margaret – Meg."</p><p>"A pleasure to meet you, Meg." Tom drew her back into the room, his thumb tracing circles over the silk of her glove. Meg pulled her hand back with another insipid giggle. It only took a few tugs to have her sprawled across the chaise, face flushing a lovely pink.</p><p>Her laughter had a panicked edge to it now, and she tried to pull back from Tom’s grip on her wrist.</p><p>"I should get back to the ball," she said, voice high and strained. "Mama will be wondering where I am."</p><p>"Oh, but we’re having such a lovely time!" Tom placed his other hand on her thigh, gripping it through her dress. "And I don’t think I’m done with you yet."</p><p>Meg’s jaw clenched. "I’ll scream!"</p><p>Tom tsked, shaking his head. "You must think of what the other guests will assume, finding you in an isolated room with a strange man." That caused her to freeze, long enough for Tom to lean forward and kiss her.</p><p>She stayed frozen, lips slack and eyes wide as he deepened the kiss and pulled one of her breasts free from her bodice. A pinch to her nipple finally stirred her to action – an offended yelp and an attempt to pull away.</p><p>"I think you should cooperate." Tom grinned at her, working her nipple between his fingers. "Think of how this would look."</p><p>Meg’s eyes shone so beautifully with tears in them. "Please, you’ll ruin me." Her voice quavered.</p><p>"That’s exactly the idea." Tom stroked her hair, pulling one of the ribbons free. "Don’t worry, I"ll make sure you enjoy it."</p><p>Meg shut her eyes and set her jaw, the serious expression at odds with her sweet face. Tom kissed her again, relishing the tiny whimper she let out, and began to work his hand beneath her skirts. She shuddered as his finger traced up the crease of her lower lips, and let out a veritable squeak when he circled around her pearl. Oh, this would be delightful.</p><p>"What are you…" Meg’s brow was furrowed, her eyes squinted in confusion at him.</p><p>"Shh," Tom said. Her legs began to quiver as he worked her pearl harder, and he feltslickness build up between her lips. She shouted as she reached her crisis – so easy, he thought – pleasure mixed with panic. "I’m giving you more than any of those fine men out there would deign to."</p><p>"I don’t want this!" Meg’s chin quivered, tears streaking her cheeks in earnest now.</p><p>"Your cunt says something different." Tom slipped two fingers of his other hand into her cunt, wet and open for him. He took her firmly but gently, feeling out which movements made her gasp and flush. Her cunt was accommodating, more so than he’d expected that of a proper lady to be. Perhaps she’d taken her own explorations, although her naivety with Morton and her sock at his actions pointed away from that. She’d certainly do so now, Tom imagined, especially after a marriage to whatever man would take her if news of this got out. Her husband would mount her and leave her aching, feeling his spend leak out of her and remembering the only man who’d had her who truly cared for her pleasure.</p><p>Meg clenched around his fingers, shaking her way through another crisis. "Please," she begged, voice cracking. "I don’t want any more, don’t touch me any more, please just leave me alone--"</p><p>She cut off when he tugged his fingers out of her cunt, much rougher than the way he’d worked them in. "You haven’t given me what <em>I </em>want yet, darling." Tom forced her skirts up around her waist, revealing her beautiful cunt, lips slick and swollen with arousal and stiffening pearl poking out from her curls. Tom spread her lips and worked his cock into her, forcing past her body’s resistance.</p><p>Meg was sobbing now – even a rich sheltered bitch like herself knew what this meant. "You’ve ruined me," she said, her voice quiet.</p><p>"I could have done so much worse." Tom pressed his lips to her neck, sucking a bruise into the tender skin there. "You should thank me for showing you how a skilled man can make you feel."</p><p>Meg turned her face away from him, pressing one tear-stained cheek to the chaise. Tom fucked her harder, making her gasp, lifting her arse off the chaise as he did so. It did shame him how quickly he reached his own climax. On another day, he could have given her a much better ride, but he’d been living rough for far too long and he hadn’t had a woman in months.</p><p>As he pulled out, Meg drew her legs up against herself, trying to right her dress. Tom grabbed her thighs and forced her back down.</p><p>"Is it sore?" Tom traced his finger around the entrance to her cunt. Meg refused to answer. "I’m going to leave you with one last gift." He knelt down at the edge of the chaise and spread her legs, licking up the crease of her lips.</p><p>"No!" Meg shrieked. "No more, please, no more…" That one scream had taken every ounce of resistance she had, it seemed; her further pleas were weak and quivering.</p><p>"Don’t worry, you’ll enjoy it." Tom locked his lips around her pearl, sucking hard. Meg bucked up against him, whimpering. It only took a few more sucks to bring her to crisis, Meg letting out a raw sob when he did so. Tom directed his attentions to her lower lips, slick with her arousal and his own spend. He pressed his tongue flat against the entrance of her cunt, soothing the stretched skin there with broad strokes. Meg squirmed against him. He slid his tongue into her cunt, enjoying the way she hissed at the intrusion.</p><p>Shouting from the hallway made him freeze. Far away yet, but he could recognize the word ‘thief’, and the blustering tone of Lord Montrose. It seemed they’d reached the ball at last. Unfortunate for Meg – if they hadn’t had reason to search the manor, her shame might have avoided notice by anyone but her mother. He hated to leave her so soon, but she’d provide a useful distraction at least.</p><p>Tom gave her perfect lips one last kiss, tugging her lovely necklace off of her neck as he did so.He shouted, "Ho, you bastards, in here!" and slipped out the window as he heard a cloud of footsteps descend on the room. If his horse wasn’t still in the stables, there would be another he could take, and by the time his pursuers had finished dealing with Meg he would be well away. A fine jewel to fence and a maidenhead – not a bad take for a night that had begun so disastrously.</p>
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